1H,4H-thieno[3,4-d][1,2]dioxine | 66642-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1H,4H-thieno[3,4-d][1,2]dioxine
• 英文别名: 1,4-dihydrothieno[3,4-d][1,2]dioxine
• CAS: 66642-70-4
• 化学式: C₆H₆O₂S
• 分子量: 142.178
• InChiKey: XTPRGJSNPDPIDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H,4H-thieno[3,4-d][1,2]dioxine 在 potassium tert-butylate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以94%的产率得到4-(Hydroxymethyl)thiophene-3-carbaldehyde
  参考文献：
  名称：

  有效合成基于双（2-氯丙烯基）硫化物的难以合成的3,4-二取代噻吩衍生物

  摘要：

  合成难以达到的3,4-二取代噻吩衍生物的有效方法：4,5,9,10-四氢噻吩并[3'，4; 5,6]-环辛基[1,2- c ]噻吩基于双（2-氯丙烯基）硫化物的连续转化，发现了1 H，4 H-噻吩并[3,4- d ] [1,2]二恶英，4-（羟甲基）噻吩-3-甲醛。无需分离中间体化合物即可实现转化。4,5,9,10-四氢噻吩并[3'，4; 5,6]环辛基[1,2- c已经基于乙酰化反应的实例研究了噻吩，并且已经显示了获得两个噻吩环参与的双官能衍生物的可能性。用X射线衍射方法研究了一些合成化合物的结构。

  DOI：

  10.1007/s10593-020-02813-2
• 作为产物：
  描述：

  3,4-二亚甲基噻吩 在 氧气 作用下， 以 二氯甲烷 为溶剂， 生成 1H,4H-thieno[3,4-d][1,2]dioxine
  参考文献：
  名称：

  杂环单峰双自由基反应的绝对速率通过纳秒时间分辨吸收光谱来确定。烯烃和双氧的二聚和环加成

  摘要：

  Singlet biradicals of the 3,4-dimethyleneheterocycle series, where the heterocycle is furan, thiophene, or N-substituted pyrrole, with chromophores in the UV-vis region (560-640 nm), are generated by nanosecond laser flash photolysis of diazene precursors in fluid solution. The rate constants for disappearance of these transients are determined by time-resolved absorption spectroscopy using the long-wavelength band. The rate constants for dimerization are near the encounter-controlled rate. Rates of trapping by alkenes are well described by a frontier orbital model. Oxygen trapping rate constants range between 10(7) and 10(9) M-1 s-1. The ratios of rate constants for trapping of 3,4-dimethylene-N-(p-toluenesulfonyl)pyrrole by pairs of alkenes in preparative competition experiments are in good agreement with those determined by the flash photolytic method. This confirms assignments of the 3,4-dimethyleneheterocycle structure to the chromophore of the biradical transients.

  DOI：

  10.1021/j100152a047

文献信息

• 3,4-Dimethylenefuran and 3,4-dimethylenethiophene, heterocyclic analogs of the disjoint non-Kekule hydrocarbon tetramethyleneethane
  作者：Keith J. Stone、Marc M. Greenberg、Joshua L. Goodman、Kevin S. Peters、Jerome A. Berson

  DOI：10.1021/ja00285a035

  日期：1986.12
• CHENG, Y. S. P.;GARRATT, P. J.;NEOH, SOON, BIN;RUMJANEK, V. M., ISR. J. CHEM., 1985, 26, N 2, 101-107
  作者：CHENG, Y. S. P.、GARRATT, P. J.、NEOH, SOON, BIN、RUMJANEK, V. M.

  DOI：——

  日期：——
• Absolute rates of heterocyclic singlet biradical reactions determined by nanosecond time-resolved absorption spectroscopy. Dimerizations and cycloadditions to alkenes and to dioxygen
  作者：Richard B. Heath、Linda C. Busch、Xu Wu Feng、Jerome A. Berson、J. C. Scaiano、Alain B. Berinstain

  DOI：10.1021/j100152a047

  日期：1993.12

  Singlet biradicals of the 3,4-dimethyleneheterocycle series, where the heterocycle is furan, thiophene, or N-substituted pyrrole, with chromophores in the UV-vis region (560-640 nm), are generated by nanosecond laser flash photolysis of diazene precursors in fluid solution. The rate constants for disappearance of these transients are determined by time-resolved absorption spectroscopy using the long-wavelength band. The rate constants for dimerization are near the encounter-controlled rate. Rates of trapping by alkenes are well described by a frontier orbital model. Oxygen trapping rate constants range between 10(7) and 10(9) M-1 s-1. The ratios of rate constants for trapping of 3,4-dimethylene-N-(p-toluenesulfonyl)pyrrole by pairs of alkenes in preparative competition experiments are in good agreement with those determined by the flash photolytic method. This confirms assignments of the 3,4-dimethyleneheterocycle structure to the chromophore of the biradical transients.
• Effective Synthesis of Hard-To-Reach 3,4-Disubstituted Thiophene Derivatives Based on bis(2-chloropropenyl) Sulfide
  作者：Valentina S. Nikonova、Nikolai А. Korchevin、Tat’yana N. Borodina、Vladimir I. Smirnov、Aleksander I. Albanov、Igor B. Rozentsveig

  DOI：10.1007/s10593-020-02813-2

  日期：2020.10

  derivatives: 4,5,9,10-tetrahydrothieno[3',4;5,6]-cycloocta[1,2-c]thiophene, 1H,4H-thieno[3,4-d][1,2]dioxine, 4-(hydroxymethyl)thiophene-3-carbaldehyde, based on consecutive transformations of bis(2-chloropropenyl) sulfide has been found. Transformations were realized without isolation of the intermediate compounds. The reactivity of 4,5,9,10-tetrahydrothieno[3',4;5,6]cycloocta[1,2-c]thiophene has been studied

  合成难以达到的3,4-二取代噻吩衍生物的有效方法：4,5,9,10-四氢噻吩并[3'，4; 5,6]-环辛基[1,2- c ]噻吩基于双（2-氯丙烯基）硫化物的连续转化，发现了1 H，4 H-噻吩并[3,4- d ] [1,2]二恶英，4-（羟甲基）噻吩-3-甲醛。无需分离中间体化合物即可实现转化。4,5,9,10-四氢噻吩并[3'，4; 5,6]环辛基[1,2- c已经基于乙酰化反应的实例研究了噻吩，并且已经显示了获得两个噻吩环参与的双官能衍生物的可能性。用X射线衍射方法研究了一些合成化合物的结构。